My answer is shaped by my interest in the authorship debate. It portrays Shakspere’s funerary monument in the Stratford church. The earlier version of the statue was sketched by William Dugdale around 1649, and lacked a quill or piece of paper. Dugdale was accurate in his sketches, printed in Antiquties of Warwickshire. There has been an unconvincing effort to discredit Dugdale, since his sketch threatens to undermine the assumption that Shakspere of Stratford was a writer.

Dugdale shows Shakspere the merchant holding a sack of wool or grain. The monument was “restored” around 1748. It appears that this “restoration” constituted an effort to re-make the merchant as a writer, implausibly showing him writing with his paper placed on a pillow.

The source of the portrait seems to be the Funerary monument of Shakespeare.
However,there are some differences between this image, and recent photographs of said monument. The quill held by Shakespeare in this engraving has been stripped bare. The recent photos of the monument show him holding a quill with the barbs still on the feather.

This reproduction is a beloved chestnut of the Stratford Shakespeare tradition. It is positive historical proof that the depicted humble Bard, jolly as a barber, was prophetic. His Charles I goatee and ‘stashe came into fashion long after bodily transport into the immortal earth.